Head of Risk & Insurance

You will lead Via's insurance program, shaping its strategy, structure, and operations, while continuing to expand it as the company takes on new business lines. Reporting to the COO, you'll be close to the parts of the business where risk shows up first. You'll own the insurance program end-to-end, partner with senior leadership on risk strategy, manage brokerage and carrier relationships, build systems and a team to manage claims and litigation, develop a broader risk management strategy, build internal infrastructure for visibility into risk, and stand up analytics to monitor program performance.

Responsibilities

• Own Via's insurance program end-to-end: assess risk profile, identify coverage needs, and put risk programs in place across markets
• Partner with senior leadership on risk strategy, including coverage decisions and alternative risk transfer
• Manage brokerage and carrier relationships: run renewals, evaluate quotes, negotiate terms, and select partners
• Build the systems and team to manage claims and litigation efficiently
• Develop a risk management strategy that goes beyond insurance, partnering with Legal and Finance to reduce loss exposure
• Build internal infrastructure: policies, processes, dashboards, and reporting for risk visibility
• Stand up analytics to monitor loss ratios, claim frequency and severity, cost per mile, and retention thresholds
• Lead, grow and develop Via's risk team as the program scales

Requirements

• Experience building and running an insurance program, ideally with significant operational exposure across multiple jurisdictions
• At least 10+ years of experience in risk management, insurance, or a closely adjacent function
• Comfort operating in ambiguity and scaling a function at a rapidly growing company
• Commercial thinking to balance insurance as both a cost and a risk management tool
• Analytical and data-driven approach leveraging claims, litigation, and operational insights
• Operational mindset to translate strategy into process, headcount, and tooling
• Hands-on and low ego approach

Benefits

• Free medical plans
• 401K matching